Reaktion #77831

Reaktionsgleichung

benzamide

benzamide N-[2-[[(1S,2S)-2-[[(4-chlorophenyl)methyl]amino]cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide

formaldehyde

→

benzamide N-[2-[[(1S,2S)-2-[(4-chlorobenzyl)(methyl)amino]cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide

Ausbeute 93.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas quenched with NaHCO3 solution
2. 2
   ExtraktionThis was extracted with EtOAc
3. 3
   TrocknenThe EtOAc was dried
4. 4
   Einengenconcentrated
5. 5
   SonstigeReverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue

Vorschrift

The title benzamide from Example 1 (21 mg) was dissolved in THF prior to the addition of Hunigs's base (0.01 mL). Next, 37% formaldehyde (0.017 mL) was added along with 4A molecular sieves. After 3 h, NaHB(OAc)3 (38 mg) was added. This mixture was stirred an additional 2 h before the reaction was quenched with NaHCO3 solution. This was extracted with EtOAc. The EtOAc was dried and concentrated. Reverse phase HPLC purification (gradient elution, water/acetonitrile/TFA) of the resulting residue provided the title benzamide N-[2-[[(1S,2S)-2-[(4-chlorobenzyl)(methyl)amino]cyclohexyl]amino]-2-oxoethyl]-3-(trifluoromethyl)benzamide (10 mg). MS found: (M+H)+=482.3.

Quelle